Vanillin → 4-isobutoxy-3-methoxybenzaldehyde

HRID 1771145Notes

Reaction equation

HRID 1771145 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]([CH3:21])[CH3:20]>CN(C)C=O>[CH3:18][CH:19]([CH3:21])[CH2:20][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium Carbonate

Product 1

HCID 6736974-isobutoxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 250 ml three necked flask, equipped with reflux condenser, mechanical stirrer, 30.4 g (200 mmol) of vanillin, 28 g (200 mmol) of dry K2CO3 and 150 ml of abs. dimethylformamide are placed in the flow of argon. The mixture is stirred for 20 min in argon condition, then 34.3 g (250 mmol) of isobutyl bromide is added. The mixture is refluxed with stirring in argon condition for 20 h at 90÷100° C., and concentrated in vacuum at 50÷80° C. to dryness. Then 200 ml of water is added to the residue, the mixture is extracted with (4×100 ml) of dichloromethane. The combined organic fraction is washed with 7% NaOH solution, dried over magnesium sulfate, filtered off, concentrated in vacuum at 50÷80° C. The residue (15 g of brown oil)-crude 4-(2-methylpropyloxy)-3-methoxybenzaldehyde is used on the next step without further purification.

Workup

  1. temperaturewith reflux condenser, mechanical stirrer
  2. temperatureThe mixture is refluxed
  3. stirringwith stirring in argon condition for 20 h at 90÷100° C.
  4. concentrationconcentrated in vacuum at 50÷80° C. to dryness
  5. additionThen 200 ml of water is added to the residue
  6. extractionthe mixture is extracted with (4×100 ml) of dichloromethane
  7. washThe combined organic fraction is washed with 7% NaOH solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered off
  10. concentrationconcentrated in vacuum at 50÷80° C
  11. customThe residue (15 g of brown oil)-crude 4-(2-methylpropyloxy)-3-methoxybenzaldehyde is used on the next step without further purification

Sources & evidence

ORD record
ord-bdb7e2433d5e4621ab36f3716ba27e03
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

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